Hydrogen Peroxide → N2-[1,1-dimethyl-2-(methyl-sulfinyl)ethyl]-N1-(2,3,4-trichlorophenyl)-1,2-benzenedicarboxamide

HRID 2358868ノート

反応式

HRID 2358868 の反応式
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].[OH-].[Na+].[CH3:15][C:16]([NH2:21])([CH3:20])[CH2:17][S:18][CH3:19].C1(=O)NC(=[O:28])C2=CC=CC1=C2.[Cl:33][C:34]1[C:40]([Cl:41])=[C:39]([Cl:42])[CH:38]=[CH:37][C:35]=1[NH2:36].OO.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCCC.C(O)=O.C(Cl)(Cl)Cl>[CH3:15][C:16]([NH:21][C:1]([C:2]1[C:3]([C:4]([NH:36][C:35]2[CH:37]=[CH:38][C:39]([Cl:42])=[C:40]([Cl:41])[C:34]=2[Cl:33])=[O:5])=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:11])([CH3:20])[CH2:17][S:18]([CH3:19])=[O:28]

参加物

13

反応物 8

HCID 784Hydrogen PeroxideHCID 6955Phthaloyl chlorideHCID 124642,3,4-TrichloroanilineHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 120973802-Propanamine, 2-methyl-1-(methylthio)-HCID 18926764Isophthalimide

生成物 1

HCID 86617046N2-[1,1-dimethyl-2-(methyl-sulfinyl)ethyl]-N1-(2,3,4-trichlorophenyl)-1,2-benzenedicarboxamide収率 89%

試薬・触媒・溶媒 4

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 284Formic Acid溶媒HCID 6212Chloroform溶媒2 回HCID 8900Heptane溶媒

反応条件

温度
20 °C

実験手順

Phthaloyl dichloride (100.0 g) was added dropwise to a mixture of aqueous sodium hydroxide solution (40.39 g/300 mL), 2-methyl-1-methylthio-2-propanamine (61.66 g) and chloroform (300 mL) at 25° C. or lower. After completion of the dropwise addition, the resulting mixture was stirred at 20° C. for 30 minutes and the organic layer was separated to prepare a solution of N-[1,1-dimethyl-2-(methylthio)ethyl]isophthalimide in 1,2-dichloroethane. The previously prepared isophthalimide solution was added dropwise to a mixture of 2,3,4-trichloroaniline (91.93 g), p-toluenesulfonic acid monohydrate (2.34 g) and chloroform (75 mL) at 60° C. and then stirred for 30 minutes. Subsequently, formic acid (2.27 g) was added thereto and then 35% hydrogen peroxide (52.66 g) was slowly dropped thereinto with heating under reflux. Thereafter, the resulting mixture was stirred at 60° C. for 3 hours. An aqueous sodium sulfite solution was added dropwise to the thus obtained reaction mixture at the same temperature to decompose the excess oxidizing agent. Then, the resulting mixture was neutralized with an aqueous sodium hydrogencarbonate solution, after which the organic layer was separated. The organic layer obtained was heated at 60° C. Heptane (800 mL) was added dropwise thereto and the resulting mixture was slowly cooled to 20° C. The crystals precipitated were filtered, washed with water and then dried to obtain 202.44 g (yield 89%) of the title compound.

後処理

  1. additionAfter completion of the dropwise addition
  2. customthe organic layer was separated
  3. customto prepare a solution of N-[1,1-dimethyl-2-(methylthio)ethyl]isophthalimide in 1,2-dichloroethane
  4. stirringstirred for 30 minutes
  5. temperaturewith heating
  6. temperatureunder reflux
  7. stirringThereafter, the resulting mixture was stirred at 60° C. for 3 hours
  8. customafter which the organic layer was separated
  9. customThe organic layer obtained
  10. temperaturewas heated at 60° C
  11. temperaturethe resulting mixture was slowly cooled to 20° C
  12. customThe crystals precipitated
  13. filtrationwere filtered
  14. washwashed with water
  15. customdried

出典と根拠

ORDレコード
ord-f2fe21bd85f34d8aaabe18d35e0dabf5
出典データセット
uspto-grants-2010_07
特許番号
US07763750B2

反応ノート

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